Triethylamine → (E)-3-(1-ethyl 3,3,5-trimethyl 2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl) acrylic acid ethyl ester

HRID 1504117Notes

Reaction equation

[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16](OS(C(F)(F)F)(=O)=O)[CH:17]=[CH:18][C:4]1=2)[CH3:2].[C:27]([O:31][CH2:32][CH3:33])(=[O:30])[CH:28]=[CH2:29].[Cl-].[Li+].C(N(CC)CC)C>CN(C=O)C>[CH2:32]([O:31][C:27](=[O:30])/[CH:28]=[CH:29]/[C:16]1[CH:17]=[CH:18][C:4]2[N:3]([CH2:1][CH3:2])[C:9](=[O:10])[C:8]([CH3:11])([CH3:12])[C:7](=[O:13])[N:6]([CH3:14])[C:5]=2[CH:15]=1)[CH3:33]

Participants

Conditions

Temperature: 180 °C

Procedure

Trifluoromethane sulfonic acid 1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl ester(0.40 g), ethyl acrylate(0.13 g), dichlorobis(triphenylphosphine) Palladium (II) (35 mg),lithium chloride(64 mg), and triethylamine(0.19 ml) were added to DMF(4 ml). The mixture was heated at 180° C. (microwave reactor) for 20 minutes. The reaction liquid was cooled to room temperature, and subjected to celite filtration. The filtrate was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate=70:30→30:70). The purified product was condensed under reduced pressure to give the title compound(0.36 g) as a pale yellow solid.

Workup

customThe reaction liquid
temperaturewas cooled to room temperature
filtrationsubjected to celite filtration
customcondensed under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane: ethyl acetate=70:30→30:70)
customcondensed under reduced pressure

Sources & evidence

ORD record: ord-5afa633bd1704e76aead6aed226fb2cb
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212187B2

Reaction notes

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